217-37-8Relevant articles and documents
Photochemical synthesis and electronic spectra of fulminene ([6]phenacene)
Okamoto, Hideki,Yamaji, Minoru,Gohda, Shin,Sato, Kaori,Sugino, Hisako,Satake, Kyosuke
, p. 147 - 159 (2013)
Facile synthesis of fulminene ([6]phenacene) was achieved through the Mallory reaction of 1-(1-naphthyl)-2-(1-phenanthryl)ethene or the 9-fluorenone-sensitized photo-ring-closure of 1-(1-naphthyl)-2-(1-phenanthryl) ethane. The electronic spectral properties of fulminene were investigated for the first time using photoluminescence as well as transient absorption spectroscopy. The spectral features were compared with those of a series of lower phenacene homologs such as phenanthrene ([3]phenacene), chrysene ([4]phenacene), and picene ([5]phenacene). For the [n]phenacene series, both the fluorescence and phosphorescence bands linearly red-shifted with an increase in the number of the benzene rings (n). Trends in the energy levels of the excited singlet (E S) and the triplet (E T) states were expressed as E s = -2.6n + 89.1 (kcal mol-1) and E T = -1.8n + 66.2 (kcal mol-1), respectively. In the case of fulminene, laser flash photolysis displayed a transient spectrum with an absorption maximum (λ max T-T) at 675 nm, which was assigned as the triplet fulminene excited state. The λ max T-T values for the [n]phenacene series showed a linear correlation as a function of the ring number n, given by an equation, λ max T-T = 60n + 318 (nm).
Efficient synthetic photocyclization for phenacenes using a continuous flow reactor
Okamoto, Hideki,Takane, Takamitsu,Gohda, Shin,Kubozono, Yoshihiro,Sato, Kaori,Yamaji, Minoru,Satake, Kyosuke
, p. 994 - 996 (2014/07/22)
The continuous flow reaction technique has been applied to the photocyclization of 1,2-diarylethenes, the so-called Mallory reaction, to afford phenacenes in high chemical yields and efficiencies (114-288mg h-1). The present technique will allow us to produce several grams of phenacenes at a time.
A New General Synthesis of Polycyclic Aromatic Compounds Based on Enamine Chemistry
Harvey, Ronald G.,Pataki, John,Cortez, Cecilia,Raddo, Pasquale Di,Yang, ChengXi
, p. 1210 - 1217 (2007/10/02)
Alkylation of enamines and enamine salts by benzylic and (β-haloethyl)aryl halides, respectively, followed by acidic cyclodehydration and dehydrogenation provides an efficient synthetic approach to a wide range of polycyclic aromatic compounds of diverse structural types.Specific polycyclic hydrocarbons synthesized by this route include benzo- and benzofluorene, 7H-dibenzo-, 13H-dibenzo-, and 13H-dibenzofluorene, 15H-tribenzofluorene, dibenzochrysene, benzopentaphene, indenofluorene, fluorenofluorene, octahydrodibenzanthracene, dibenzanthracene, octahydrodibenzanthracene, dibenzanthracene, picene, benzopicene, 1H-benzaceanthrylene, and 4H-cyclopentachrysene.This method with appropriate modifications appears to be potentially broader in scope than established traditional methods of polycyclic hydrocarbon synthesis.